Mike Milken

Mike Milken entered the world appropriately enough on July 4, a date that to American ears positively screams clean slates and fresh starts. His affinity for figures was apparent early on; he helped his accountant father fill out tax returns as a kid. A graduate of Wharton Business School, Milken would go on to essentially invent the market for “junk,” or high yield, bonds while at Drexel Burnham Lambert. A workaholic, he was typically ensconced in his office from 4:30 a.m. until 7:30 p.m, and such was Milken’s innate talent that 17 years of trading reputedly encompassed a mere four losing months. Junk bonds utterly altered the way corporate America raised capital, gave birth to the culture of Wall Street corporate raiders in the 1980s, and funded the breakneck growth of companies including MCI Communications, Viacom (NASDAQ:VIA)  and Turner Broadcasting. Ted Turner himself called Milken “smarter than a tree full of owls" while the Washington Post lauded the Californian as "the most influential financier of the postwar era."

For someone who came to symbolize the excesses of the Gordon Gekko “greed is good” leveraged-buyout era, Milken remained “painstakingly modest" according to Connie Bruck, whose Predators’ Ball chronicled his rise and fall. Indeed the financier famously eschewed a corner office suite for an iconic X-shaped trading desk, which was reconstituted when Milken moved his operation from New York to Beverley Hills on, yes, Independence Day in 1978. That desk marked the spot where, in 1986, he helped make a hitherto unheralded investment boutique, which was perennially in the slipstream of Goldman Sachs (NYSE:GS) and Morgan Stanley (NYSE:MS), the single most profitable institution in the entire history of Wall Street. One year later Milken personally took home a paycheck that, even now, appears faintly preposterous -- $550,054, 000, or, as the Wall Street Journal noted, more than it cost to send the space shuttle into orbit.
 

In 1989 the gravy train came to an abrupt end when, with investor appetite for junk bonds collapsing and the savings and loan crisis starting to swirl, an aggressive prosecutor on the rise named Rudolph Giuliani, then United States Attorney for the Southern District of New York, filed a 98-count, 110-page indictment. The government’s allegations included insider trading and racketeering charges related to myriad hostile takeovers and corporate restructurings. Milken plead guilty to six counts of securities fraud in 1990 (Drexel Burnham not coincidentally went belly up that same year), was hit with well over $600 million in fines, and received a lifetime ban from the securities industry. He entered prison in March 1991, sentenced to 10 years yet eventually serving “only” 22 months. (I say “only” as by all accounts it wasn’t the celebrity tennis camp of popular imagination. One report had the Feds trying to break a man who even his enemies admitted was a genius, evil or otherwise, with soul-destroying assignments which included filling salt shakers.)

The erstwhile tycoon was eventually released to a Los Angeles halfway house on January 3, 1993, which is where the story really gets interesting. Days after being sprung from jail, Milken was diagnosed with prostate cancer and given at most 18 months to live. The former felon’s redemption song soon began in earnest, with a second act which would eventually prove even more successful than his first claim to fame. That same year he established the Prostate Cancer Foundation, ultimately transforming awareness of the disease to such an extent that Fortune magazine would one day hail him, without accusations of hyperbole, as “The Man Who Changed Medicine.” A longstanding charitable streak -- the Milken Family Foundation was founded as far back as 1982 -- came more to the fore, as did assorted “do-gooder” investments in educational outfits including LeapFrog Enterprises (NYSE:LF) and Knowledge Universe. Above all, the Milken Institute has morphed into a sort of Stateside Davos, where moguls come not merely to pontificate but exchange ideas of genuine consequence. And, irony of ironies, when the man who was now New York mayor and a serious presidential aspirant succumbed to prostate cancer himself in April of 2000, Rudy Giuliani and the person he put behind bars struck up the unlikeliest of alliances. Indeed Hizzoner even went so far as to say the erstwhile object of his ire should receive a presidential pardon, as indelibly described in an article that won its author a Pulitzer Prize in 2001. (Little wonder that the committee opted not to bestow an award for fiction last year, for who needs fantasy when fact is infinitely more implausible?)

Thus ends, at least for now, the remarkable transformation of Michael Robert Milken, whom time has turned from toupee-wearing convicted felon to bald elder statesman of philanthropy. His many powerful allies always asserted that the financier was guilty of no more than making enormous sums of money, and was witch-hunted by overzealous lawyers for “crimes” unworthy of the name. Not all share that view of course, but vindication is the best revenge for the 66-year-old whose estimated net worth now stands in the neighborhood of $2 billion. Junk bonds have swiftly followed up a stellar 2012 with what the Journal just characterized as a “record-breaking start to 2013.” And compared with the outright criminality of much that came later -- from Enron to Worldcom to dot-com, Lehman Brothers to the brothers Madoff -- Mike Milken increasingly looks like a Boy Scout by comparison. He may have broken the rules, but unlike many entries in our financial rogue’s gallery, never personally lost anyone a dime.

Henry Blodget

''I expect my obituary will read, ‘Henry Blodget comma who predicted Amazon would hit $400 comma.'"

So the onetime star stock analyst told the New York Times in March 2001, but life has a strange way of upending easy assumptions. Bill Clinton -- president during the 1990s Internet boom that gave birth to Blodget and his ilk -- surely similarly fretted that the first line of his obit would say, “Only the second president to be impeached comma.” It still may, but 14 years to the week after his trial started in the Senate, Monica is but a distant memory for the original “comeback kid,” who freshly finds himself on a list of the planet’s most admired people. Henry Blodget did indeed initially make his name, and earned a money-spinning move to Merrill Lynch, with a prophecy that Amazon (NASDAQ:AMZN) would reach $400 per share in late 1998, during the heady days of the Internet bubble. Yet there is so much more to the story. A subsequent investigation by then-New York Attorney General Eliot Spitzer unearthed damning email evidence of the researcher issuing official “Buy” recommendations on the same stocks he privately disparaged, all with the intent of securing lucrative investment banking business for the firm. One infamous instance included the notation "POS," not in its present text message meaning of “Parent Over Shoulder,” but instead used to internally characterize a publicly-lauded stock as a “Piece Of Sh%t.”
 

Blodget, blasted for issuing misleading reports “for which there was no reasonable basis” over a two-year period, was subsequently banished, much like Milken, from the securities industry for life. A $4 million fine followed -- his annual salary was estimated at $12 million -- although it was absent any outright admission or denial of guilt. In November 2001, with smoldering rubble from the terrorist attacks of two months earlier still visible from his office across the street, the analyst opted, like many on Wall Street at that troubled time, to reassess what was ultimately important. He accepted a buyout package on offer, adding in classic ‘second acts’ style, “It just seemed like a good time to pursue the next thing." (Full disclosure: During this period I worked in the equity research unit that served as a liaison between stock analysts and Merrill’s 15,000 strong army of financial advisors, many of whom fielded furious inquiries from irate clients as the dot-com era came crashing down. These calls were quickly transferred over to us, and for a spell it seemed as if our department’s sole purpose was to play the role of a fire hydrant at a dog convention. Yet personally I always found Henry nothing but nice. Indeed he made a point of sending us all a bottle of wine for Christmas 2000, along with a note saying, “Sorry for all the trouble I’ve caused you guys this year.” Interestingly, his holiday gift to clients in 1998 was Extraordinary Popular Delusions and the Madness of Crowds by Charles Mackay, suggesting that the analyst was well aware we were witnessing nothing more than another one of Mr. Market’s periodic bouts of tulip mania.)
 
Feeling, in his formulation, like a “global piñata,” Blodget mulled the next step. As it happened, the following chapter involved writing a book, The Wall Street Self-defense Manual in 2007, before eventually co-founding the influential financial website Business Insider, where he is currently CEO and Editor-in-Chief. The product, while too tabloid for some tastes, has quickly become an indispensible read for many in the industry, and both its revenue and roster of upscale advertisers continue to increase apace. The years since the scandal broke have been kind to Henry Blodget. Being banned from the securities industry for all time hasn’t stopped him from becoming an unlikely Salvation Army of sorts for the NYSE, ringing bells there to officially begin proceedings in both 2011 and 2012. This one time poster child for all Internet excess now finds himself frequently wheeled out as an experienced voice of reason on CNBC, sagely offering advice to a new generation of investors. Occasionally, as when hailing Mark Zuckerberg as an “improbably brilliant CEO” in a New York magazine cover article only four days before a spectacularly botched IPO indicated otherwise, he can still stand accused of being a cheerleader for money-losing web ventures. Yet accumulating evidence indicates that Blodget is hardly alone here and, fully a decade on, the jury is decidedly still out on Eliot Spitzer’s attempt to reign in overly rosy research recommendations.

Ah, Eliot. Ironically, just as Mike Milken and his earlier arch nemesis Rudy Giuliani subsequently became the strangest of bedfellows in their second act, so have Henry Blodget and the man who once attempted to end his career since kissed and made up. "I really thought he was on course to being president of the United States,” Blodget told Bloomberg, although any such ambitions abruptly ended after the prosecutor’s dalliance with a prostitute as the notorious ‘Client Number 9.’ For his part, Spitzer cooed in an interview with the same publication,"Listen, I think Henry’s great." Indeed in 2009 the two men even came together for a remarkably cozy breeze-shooting session, a confab characterized by Gawker as ‘Blodget v. Spitzer: Disgraced Rich White Men Sit Down for a Chat.’

Cynics may say Henry Blodget’s second act as a financial journalist is ultimately just an extension of what he always was. That the onetime proofreader for Harper’s magazine, armed only with a humanities degree, literally had no business dispensing business advice, and merely rode one of Wall Street’s historic waves. Others see his resurgence as an inspiration. Either way, it makes for a fascinating narrative, and the final few exciting chapters are still to be written.
 

Martha Stewart
 
Second acts? The former Martha Helen Kostyra has reinvented herself more often than Madonna. Prior to becoming the world’s best known domestic diva, she shilled soap for Unilever (NYSE:UN) in the 1950s, dabbled in modeling during the Swinging Sixties, and, for seven years ending in 1972, worked as an account executive at Wall Street firm Monness, Horstman, Williams, and Sidel, exiting the industry at age 32. The bicentennial year saw Stewart start a catering business in her basement before eventually releasing her first book, Entertaining, in December 1982. Her timing was as impeccable as her taste, for that very month US unemployment topped out at 10.8%, the highest rate since the Great Depression. The Dallas and Dynasty opulence of the Age of Reagan was about to begin in earnest, and Stewart’s elegance exerted enormous aspirational appeal to a nation newly embarking upon the longest peacetime economic expansion in its history. Martha Stewart Living, a quarterly magazine, arrived on the scene in 1990 under the aegis of Time Inc, and her burgeoning business empire ultimately became Martha Stewart Living Omnimedia (NYSE:MSO) in September 1997. Its very name testified to the ubiquity of Brand Martha, whose properties in time came to encompass television, print, and all manner of ancillary merchandise. By both good luck and design, the company went public at the end of 1999, just as the stock market’s millennial madness reached apogee.
 
The fall, when it arrived, was as spectacular as her ascent had been, and came accompanied by an outbreak of schadenfreude from the many critics gleeful at seeing this perfectionist Stepford Housewife get an overdue comeuppance. Ironically, Stewart’s Icarus moment involved an imprecise reading of the same securities laws she should have been intimately acquainted with in light of her prior incarnation as a stockbroker. The SEC determined she indulged in insider trading with a suspiciously well-timed sale of biotech outfit ImClone Systems during December 2001. Two years later the authorities indicted Stewart on nine counts, ranging from obstruction of justice to outright fraud. Found guilty in March 2004 of charges including conspiracy and providing false statements to federal investigators, she was sentenced in July 2004 to five months in jail. Overnight, one of the wealthiest and most well-known women in America answered to the name of prisoner number 55170-054.  The salad days thus appeared all over for a celebrity who, in a surreal interview on national television while the investigation was ongoing, actually wielded a knife while saying "I just want to focus on my salad."
 
And yet. Only 12 months after her 2005 release, Martha Stewart Living Omnimedia -- which experts said was utterly incapable of surviving the incarceration of its animating force -- returned to profitability. Advertisers flooded back, books and business ventures followed, and new TV shows aimed at image rehabilitation were rolled out, including a special version of The Apprentice.  Even competitor Oprah Winfrey, whose O Magazine lost neither love nor shelf space to Martha’s own glossy on the newsstands, hailed her “incredible comeback” in 2010. 2011 saw Stewart’s return to the board of directors, and last year she again ascended to its chairmanship. But surely the most satisfying, and certainly surprising, second act for this septuagenarian “Suzy Homemaker” is her most recent role as the unlikeliest of Web-savvy inspirations to a new generation of 20-something hipsters from Williamsburg. Indeed in a CNBC interview on Monday, Ms. Stewart proudly pointed out of her publications "We’re the most ‘pinned’ magazines on Pinterest right now," adding she attracts “almost 3 million followers on Twitter.”
 
“Martha’s Mess” read the front cover of Newsweek at the height of her scandal. Ms. Stewart ultimately enjoyed the last laugh however, certainly on that publication, which has just embarked upon its own desperate second act as an online-only magazine. For Martha’s legion of fans, her revival is indeed “a good thing.”
 

Jamie Dimon
 
Jamie Dimon’s path to the top was an especially circuitous one, its ascent never actually encompassing a revenue-producing position on Wall Street. His paternal grandfather Panos Papademetriou arrived in New York from Greece just as the Twenties really started to roar. Dimon himself grew up relatively humbly in Queens but was imbued with an immigrant’s hunger and graduated from Harvard Business School precipitously enough in 1982, when the biggest bull market in history began. He thus embarked upon a 16-year working relationship with fabled financier Sandy Weill, first at American Express (NYSE:AXP) and later while cobbling together the myriad companies which would one day become financial giant Citigroup (NYSE:C). Weill initially took almost paternal care of his protégé, even going so far as to make him president of Citi predecessor firm Primerica in 1991, relinquishing the title to the 35-year-old wunderkind in the process. Yet this tale of two mountainous egos was destined to end in tears. No sooner had the ink dried on the duo’s crowning $9 billion deal to buy Salomon Brothers in 1997 than the end game played out as Wall Street’s most widely-watched soap opera. The sandbox psychodrama saw Weill blow his top at Dimon’s stubborn refusal to promote the elder man’s daughter, and take serious offence at a New York Times photograph showing Dimon strutting front and center, while the senior partner pointedly paced several steps behind. At the prestigious Greenbriar Resort in November 1998, Weill finally fired a man he saw as casting overly covetous eyes on his own CEO position, with the two reputedly almost coming to blows during the dramatic dénouement.
 
Dimon, his hitherto meteoritic rise at an abrupt end, spent the ensuing 18 months unemployed, adrift, and in exile. The onetime rising star was quickly cast aside, fatally seen as yesterday’s man in an industry where being even temporarily out of the loop is often tantamount to a kiss of death. He rejected an overture from Amazon and was, for a time, viewed as a viable candidate for the top job at Home Depot (NYSE:HD). Real redemption, however, only arrived in March of 2000 -- the very month the stock market topped out -- when Dimon became head of Chicago’s Bank One. His five years at the helm turned an ailing organization into one which JPMorgan (NYSE:JPM) was sufficiently impressed with to acquire for $58 billion. The New Yorker’s chastening experience at Citigroup now but a bad dream, Dimon in turn ascended to the top of America’s biggest bank. His attention to detail was the stuff of legend, and in 2008, the CEO cemented a walk-on-water reputation among Wall Street peers by basically rescuing capitalism from itself. In March of that fateful year Dimon famously picked up a beleaguered Bear Stearns for less than it cost to buy David Beckham. Six months on he was hailed as a hero for keeping Washington Mutual afloat as financial calamity raged all around it. In a tale worthy of Dickens, the worst of times for American finance truly was the best of times for one James Dimon.
 

Apple (NASDAQ:AAPL)
 
We end not with a person but an entire company, although the individual most closely associated with it endured and enjoyed a similarly spectacular roller coaster ride. Impossible as it is to believe now, a decade and a half ago Apple Inc. was in the doldrums. Its market share in US personal computers, at 15.1% second only to International Business Machines (NYSE:IBM) in 1985, stood at a scant 7.9% ten years on. Not only was its principal product relegated to also-ran status, its few remaining adherents found primarily in niche educational markets and not taken at all seriously by Corporate America, but Apple’s Newton digital assistant also ended up being an unmitigated disaster. Even the company’s flagship Mac offering, introduced to much fanfare in an iconic Super Bowl ad, never actually attained anything like the commercial success of hazy hindsight. Its stock subsequently missed out entirely on a 1990s bull run that saw an astonishing 89,374% increase in rival Dell Inc. (NASDAQ:DELL), whose bare bones, direct-to-consumer approach was the anthesis of the touchy-feely in-store experience Apple would ultimately adopt amid widespread skepticism.
 
Indeed its share price plunged to as low as $3.30 in the summer of 1997, when one Steve Jobs was summoned back in a move that smacked to some as sheer desperation. Jobs himself had lost a boardroom battle at his own firm a dozen years earlier, squeezed out by John Sculley, and with the intervening rust Wall Street wondered aloud whether he was the right man to stem quarterly losses that stood at some $708 million. “The products SUCK -- there’s no sex in them,” was the prodigal son’s candid assessment upon his return. Yet with the Cupertino company bleeding red ink at an alarming rate and only three months from bankruptcy, salvation soon arrived via the sort of unlikely pairing that seems to occur unusually often in second acts. Arch nemesis Microsoft (NASDAQ:MSFT), in a move Bill Gates must now regret, invested $150 million in Apple thanks to the persuasive powers of Mr. Jobs and the rest is, well, his story. Truth be told, it took Apple over a decade to become today’s overnight sensation, but once the firm finally returned to profitability in 1998 after 12 barren years, the hits simply didn’t stop. Starting with that spring’s introduction of the iMac, Apple steadily began either upending or altogether inventing entire industries. iPod (2001), iTunes (2003), iPhone (2007), and iPad (2010) all followed in swift succession until, in August of 2012 Apple attained a market capitalization of $624 billion, the highest in the history of the world. Sadly, Steve Jobs didn’t live long enough to see it, but the visionary would doubtless have enjoyed the ironic identity of the fallen tech titan whose crown Apple had usurped. It was none other than Microsoft, whose stock surged 9,566% in the 1990s en route to hitting its peak during the dying days of a decade in which pesky upstart Apple barely registered as an afterthought. For Apple, making its hated corporate cousin subsequently look like a sad second banana was surely the sweetest second act of all.

Twist in the Tale
 
"There are no second acts in American lives."
 
The F. Scott Fitzgerald quote always troubled me. After all, we Americans -- often immigrants who have left the past behind specifically to start afresh -- are all about constant renewal. And Fitzgerald himself gave voice to Gatsby, the very epitome of reinvention. I turned to an English literature expert of my acquaintance for further clarification, and was reliably informed that the author did not, as is mistakenly assumed, mean for one moment to imply that second chances aren’t readily available in this country. Rather, in a traditional play structure, act one sets the scene, and by the second act we are at least starting to move toward some sort of resolution. Fitzgerald, however, maintained that, in the United States, nothing is ever neatly resolved and tied up in red ribbons. (Fittingly the line comes not from The Great Gatsby but The Last Tycoon, his final and pointedly unfinished novel.)